That is both a literal and figurative question. To what lengths would you go and what distance would you travel to do something you’ve dreamed of?

Max Pezzali!

In April I did one of the most spontaneous, exciting and gratifying things I’ve ever done: I bought a concert ticket to see my favorite Italian singer. In Italy. With two weeks lead time.

Max, Nek and Renga. Singing along in the Verona amphitheater. #pinchme

Call me crazy (pretty sure my husband did), but it was SO MUCH FUN! And really, he was totally supportive and had fun watching me have fun – and I really had the time of my life. Have you ever “gone so far” with spontaneity? I’d love to hear!

It actually came together just like it was meant to be. Concert ticket, airline tickets, appointments with guides and wineries in Verona (I worked a little too) and then meeting my husband in Prague, Czech Republic, where he was for work. It was worthwhile for Cypress Tours and also soul-nourishing as I feed my wanderlust fire.

Valpolicella wine region near Verona

I highly encourage travel and adventure for so many reasons. Personally, I get a thrill that’s hard to beat when experiencing a different place, culture, food, language. Food-travel host Anthony Bourdain earlier this year said on Time.com: “The idea of staying local—be it in a charming hotel or B&B—can help drive those unexpected moments and then some. I want to find a hotel in a neighborhood that has charm and character—the sort of place where I can walk to a café, sit down, and feel the place. You can’t take it in, driving by stuff. That’s not satisfying,” he says. “Travel moments can be magical.” That’s what I’m after for my guests and me – the life-changing, soul-touching magic of experiential travel.

My new friend Sara. I met her and her husband at dinner. Max fans!

I think that’s one of the things I love about taking groups on these adventures: I see it in your eyes and in your enthusiasm – and I experience it all over again through you. I love to make these turn-key opportunities become your travel-adventure reality.

Speaking of groups and adventures, I’ve taken 30 beautiful souls to Italy this year: Tuscany, Rome and the Amalfi Coast.

Looking ahead at 2019, I have growing lists for more locations in February, May, August, September and October: we’ll be in the north – Tuscany (Viareggio) and the Veneto (Verona, Venice) regions and again south, with stops in Umbria (Orvieto) and Campania regions (Pompeii and Positano.)

Please let me know if you’d like to be added to a list and I will keep you apprised. Everything for 2018 was sold out, but we have time to plan for 2019. Early signers get input on the itineraries!

It takes 90 seconds for the horses to run three laps in the Palio horse race in Siena. But it takes weeks of preparation and parties to get there. “il Palio” is held twice a year: July 2 and August 16; both are celebrations around the Virgin Mary.

Image from above of the race course, crowd and the clam-shell-shaped Campo Square.

Ten horses are drawn by lottery to run for 10 of the 17 neighborhoods, or contrade, in Siena. Truckloads of dirt are placed around the edges of the main town square, il Campo, to create a racetrack. As the race nears, 10 jockeys also are drawn by lottery for the bare-back competition. Practice races are run, parades and pageantry are held, and then things get serious.

Banner for the August Palio in 1750.

Betting, bribing and strategy dominate the days leading up to the important race. The winning jockey could earn a nice wage. The winning horse is revered. In fact, a horse without a jockey can win, which happened recently at the Oct 20 “Extraordinary Palio.” And most important: the winning contrada earns bragging rights. The victorious neighborhood gets to fly their flag throughout their streets – and party like rock stars until the next race is run and a new winner takes over.

Bleachers fill up and crowds of people line the streets. Attendees flock to the center of the Campo Square to be in the middle of the excitement and be ready to celebrate the winner. But once inside, the square is sealed off; they stand, wait, watch, revel – for hours. You don’t eat, drink or have access to facilities.

Inside the normally quiet Campo Square. Great hang-out spot to sit, picnic, catch up with friends.

However; there are more comfortable options available to watch the race, like private balconies – and I’d like to take a small group for this experience. It’s a once-in-a-lifetime event!

Through my friend in Siena, I have balcony seats reserved for the August race. We’ll have a buffet, beverages and – most luxurious – a private bathroom.

I am taking reservations now for this trip Aug 11-21, 2019, where we’ll watch the race on Aug. 16. In addition to this memorable and rare spectacle, we’ll also have a full cultural experience: visit Tuscan wineries, enjoy a cooking lesson and traditional meals, take private tours, stay in a countryside villa and more.

There are only 8 spots available (four left as of 11/5/18) for this exclusive tour, so please let me know ASAP if you’d like to join the adventure.

I share a birthday with Andrea Bocelli. I’m not sure he knows it, but if I run into him in Tuscany, I’ll spill. On Sept. 22 he turned a young 60. He was born in Lajatico, Tuscany and now lives in Fortei di Marmi – not far from Viareggio, where we’ll be in February and May.

I’ve come across a couple things recently that are share-worthy. Not only is he a super talented tenor, but he’s a very thoughtful and down-to-Earth human being.

Blind since age 12, he thought nothing of windsurfing, skiing and skydiving. He doesn’t look at physical limitations the way you might think. “There is no impossible dream. If you have enough faith, discipline and humility, you can pursue just about any task.”

His 20-year-old son, Matteo, sings with him on his latest album. A friend recently sent a video of their song “Fall On Me”, which is so beautifully done. They sing to and about each other, and it includes old family photos. Very touching! (Celine Dion has said that “if God would have a singing voice, he must sound a lot like Andrea Bocelli.) He’s extremely proud of his son’s talent, but also says he wants Matteo to chart his own course. “I know how much pressure there is and how many setbacks there can be. You want what’s best for your children, even though they need to find their own way.”

He has sung duets with countless singers from around the world during his nearly 30-year career, including his manager-wife, Veronica. He actually has a law degree from the University of Pisa (’87) and practiced law one year before taking a fork in the road that led to his magnificent singing career.

And in a world that can be so dark and negative, it’s easy to say no – to requests, to concerts, to many things. But yes is so much better, he says. “You say yes when you have your first kiss, when you want to make someone feel good, when you open yourself to new experiences. I always say yes – sì, sì, sì! – and it makes every day better.” The title of his new album, out this month, is titled Sì.

One last cool fact: In 2006, Bocelli worked with his hometown Lajatico to build an outdoor theatre, the “Teatro del Silenzio.” He serves as its honorary president and performs for one night only, every July; the rest of the year, the theatre remains silent. He invites others to join him each year, like Italian performers Placido Domingo and Laura Pausini and American jazz musicians Chris Botti and Kenny G.